1. Field of the Invention
The present invention relates to new and valuable phenyl piperazine compounds and more particularly to 1,4-substituted phenyl piperazine compounds of noteworthy therapeutic utility and to a process of making and using same.
2. Description of the Prior Art
ARCHER in U.S. Pat. No. 3,062,821 discloses 1,4-disubstituted-2-piperazinones of Formula I ##SPC1##
in said formula
R represents lower alkyl; PA1 X and X' represent hydrogen, lower alkoxy, or hydroxyl; and PA1 Y hydrogen or lower alkyl. PA1 R.sub.1 is hydrogen, alkyl, cycloalkyl, aralkyl, alkyl substituted aralkyl, diaminoalkyl, or furfuryl; PA1 R.sub.2 is hydrogen or methyl; PA1 R.sub.3 is hydrogen, alkyl, cycloalkyl, phenyl, naphthyl, alkyl, chloro, or alkoxy substituted phenyl or naphthyl, aralkyl, alkyl sustituted aralkyl, or 2-furyl; PA1 R.sub.4 is hydrogen or alkyl; and PA1 R.sub.5 is hydrogen or alkyl. PA1 R is alkyl, tertiary aminoalkyl, or aralkyl; and PA1 R' and R" are hydrogen or lower alkyl. PA1 X, y, and Z are the same or different substituents and may be either hydrogen, halogen, trifluoro lower alkyl, preferably trifluoro methyl, hydroxyl, lower alkoxy, preferably methoxy or ethoxy, or phenyl substituted lower alkoxy, such as benzyloxy; PA1 R is di-(lower)alkylamino (lower)alkyl, and preferably dimethylamino ethyl, diethylamino ethyl, dipropylamino ethyl, dimethylamino propyl, diethylamino propyl, di-n-propylamino propyl, or lower alkyl substituted by one or two saturated monocyclic heterocyclic rings such as piperidino, pyrrolidino, piperazino, N-lower alkyl piperazino, 3-ketopiperazino, morpholino, or the like, preferably piperidino ethyl, morpholino ethyl, or dimorpholino propyl; PA1 R.sub.1 is lower alkyl with 1 to 3 carbon atoms; and ##EQU1## is the group ##SPC6## PA1 One halogen atom in 2-; 3-; or 4-position. PA1 Two halogen atoms in 2,3-; 2,4-; 2,5-; or 3,4-position and, if desired, also in 2,6-position. PA1 R.sub.3 is hydrogen or a saturated five- or six-membered heterocyclic ring, preferably the morpholino ring attached by its heterocyclic nitrogen atom to the lower alkyl R.sub.2 ; and PA1 R.sub.4 and R.sub.5 are lower alkyl or, together with the nitrogen atom to which they are attached, form a saturated five- or six-membered heterocyclic ring, such as the pyrrolidino, piperidino, piperazino, or morpholino ring. The piperazino ring may be substituted at its other nitrogen atom by lower alkyl or by hydroxy lower alkyl to represent the N.sub.4 -lower alkyl or N.sub.4 -hydroxy lower alkyl piperazino ring or it may be substituted by a keto group to represent the 3-keto piperazino ring. PA1 X.sub.1 is hydrogen or lower alkoxy. PA1 Y.sub.1 and Z.sub.1 are hydrogen, halogen, trifluoromethyl; hydroxyl, lower alkoxy, and phenyl lower alkoxy, whereby X.sub.1 is lower alkoxy only if Y.sub.1 and Z.sub.1 are lower alkoxy; PA1 R.sub.1 is lower alkyl with 1 to 3 carbon atoms; PA1 R.sub.2 is lower alkyl; PA1 R.sub.3 is hydrogen or a saturated five- or six-membered heterocyclic ring, said heterocyclic ring being attached by its heterocyclic nitrogen atom to the lower alkyl R.sub.2 ; PA1 R.sub.4 and R.sub.5 are lower alkyl or, together with the nitrogen atom to which they are attached, form a saturated five- or six-membered heterocyclic ring. PA1 1-(4-Chloro benzyl)-2-phenyl-3-keto-4-(diethylamino ethyl) piperazine; PA1 1-(4-chloro benzyl)-2-phenyl-4-(diethylamino ethyl)piperazine; PA1 1-(3,4-dichloro benzyl)-2-phenyl-4-(diethylamino ethyl)piperazine; PA1 1-[(4-methoxy phenyl)-ethyl]-2-phenyl-4-(diethylamino ethyl)-piperazine; PA1 1-[3-phenyl propyl-(1)]-2-phenyl-4-(diethylamino ethyl)-piperazine; PA1 1-(4-chloro benzyl)-2-phenyl-4-(piperidino ethyl) piperazine; PA1 1-(4-chloro benzyl)-2-phenyl-4-[1,3-dimorpholino propyl-(2)] piperazine; PA1 1-(4-chloro benzyl)-3-phenyl-4-(diethylamino ethyl) piperazine. PA1 X, y, z, and R.sub.1 represent the same substituents and numerals as given hereinabove, while PA1 Hal is halogen. PA1 Hal is halogen and R represents the above given substituent.
Said 1-[2-(phenyl lower alkyl)]-4-lower alkyl-2-piperazinone compounds are useful intermediates in the preparation of compounds of Formula II ##SPC2##
in which R, X, X', and Y represent the same substituents as given hereinabove. These 1-[2-(phenyl lower alkyl)]4-lower alkyl piperazine compounds are useful hypotensive agents.
DE BENNEVILLE in U.S. Pat. No. 3,390,139 discloses N-vinyl-2-piperazinones of Formula III ##SPC3##
in which
These compounds are polymerizable or copolymerizable compounds, the resulting polymers or copolymers are useful for many purposes. Higher members of the monomeric N-vinyl-2-piperazinones of Formula III show fungistatic and bacteriostatic activity and are useful for other purposes.
DE BENNEVILLE in U.S. Patent No. 2,653,153 describes 4-N-substituted-2-ketopiperazines of Formula IV ##SPC4##
in which
These 4-N-substituted-2-ketopiperazines are valuable activators and synergists for insecticidal agents.
None of these compounds has found any noteworthy application in veterinary and human therapy.